4-Hydroxy­benzoic acid–1H-imidazole (1/1)

Wang, W.; Liu, B.-W.; Liu, J.; Ren, R.

doi:10.1107/S1600536809016043

organic compounds

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Volume 65| Part 6| June 2009| Page o1205

doi:10.1107/S1600536809016043

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4-Hydroxybenzoic acid–1H-imidazole (1/1)

Wei Wang,^a Bang-Wei Liu,^b Jing Liu ^b and Rui Ren ^a ^*

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, 210009 Nanjing, Jiangsu, People's Republic of China, and ^bCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, 266042 Qingdao, Shandong, People's Republic of China
^*Correspondence e-mail: greeneese@163.com

(Received 19 April 2009; accepted 29 April 2009; online 7 May 2009)

In the title 1:1 adduct, C₇H₆O₃·C₃H₄N₂, the crystal packing features π–π stacking interactions [centroid–centroid distances = 3.799 (2) and 3.753 (1) Å] as well as N—H⋯(O,O) O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Li et al. (2005 ); Wan et al. (2005 ). For the synthesis, see: Wang et al. (2006 ). For bond-length data, see Allen et al. (1987 ).

Experimental

Crystal data

C₇H₆O₃·C₃H₄N₂
M_r = 206.20
Monoclinic, P 2₁ /n
a = 9.601 (2) Å
b = 10.530 (2) Å
c = 10.586 (2) Å
β = 113.759 (3)°
V = 979.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.47 × 0.29 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.955, T_max = 0.987
5200 measured reflections
1858 independent reflections
1583 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.213
S = 1.11
1858 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.53	3.057 (3)	121
N1—H1⋯O2	0.86	1.82	2.678 (3)	177
O3—H3⋯O1ⁱ	0.82	1.83	2.635 (3)	166
C8—H8⋯O1ⁱⁱ	0.93	1.89	2.748 (3)	153
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016043/at2768sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016043/at2768Isup2.hkl

checkCIF report

Comment top

Imidazole compounds have received considerable attention in the literature. We have reported the structure of 3-(1H-imidazol-1-yl)-1-phenylpropan-1-one, (II) (Li et al., 2005). In order to obtain comprehensive structural information of imidazole compounds and in our ongoing search for new imidazole compounds, the title compound, (I), was prepared hydrothermally and we report its structure here.

A view of the molecule of the title compound, (I), is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The bonds in the imidazole and hydroxybenzoate systems show intermediate character between single and double bonds, indicating a highly π-conjugated delocalization. The crystal structure is stabilized by π–π interactions involving the imidazole and hydroxybenzoate rings: Cg1···Cg1 (-x, 2 - y, 1 - z) = 3.799 Å and Cg1···Cg2 (-x, 1 - y, 1 - z) = 3.753 Å, where Cg1 and Cg2 denote the centroids of the N1/N2/C7—C9 imidazole and C1—C6 benzene rings, respectively. In the crystal packing, molecules are linked into three-dimension network by C—H···O and O—H···O intermolecular hydrogen bonds (Table 1).

Related literature top

For related structures, see: Li et al. (2005); Wan et al. (2005). For the synthesis, see: Wang et al. (2006). For bond-length data, see Allen et al. (1987).

Experimental top

The title compound was prepared according to the literature method of Wang et al. (2006). It was hydrothermally prepared from a reaction mixture of CdCl₂.2.5H₂O, 4-hydroxybenzoic acid, 1H-imidazole, and distilled water (10 ml) in a molar ratio of 1:2:6:555. The mixture was stirred for 20 min at room temperature and then crystallized in a Teflon-lined stainless steel autoclave with a 23 ml capacity at 433 K for five days. After cooling, single crystals of (I) suitable for X-ray measurements were obtained.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.

4-Hydroxybenzoic acid–1H-imidazole (1/1) top

Crystal data top

C₇H₆O₃·C₃H₄N₂	F(000) = 440
M_r = 206.20	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2125 reflections
a = 9.601 (2) Å	θ = 2.9–25.6°
b = 10.530 (2) Å	µ = 0.11 mm⁻¹
c = 10.586 (2) Å	T = 293 K
β = 113.759 (3)°	Block, colourless
V = 979.6 (4) Å³	0.47 × 0.29 × 0.10 mm
Z = 4

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	1858 independent reflections
Radiation source: fine-focus sealed tube	1583 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.7°, θ_min = 2.4°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
T_min = 0.955, T_max = 0.987	l = −12→5
5200 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.213	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.1212P)² + 0.6043P] where P = (F_o² + 2F_c²)/3
1858 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₇H₆O₃·C₃H₄N₂	V = 979.6 (4) Å³
M_r = 206.20	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.601 (2) Å	µ = 0.11 mm⁻¹
b = 10.530 (2) Å	T = 293 K
c = 10.586 (2) Å	0.47 × 0.29 × 0.10 mm
β = 113.759 (3)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	1858 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1583 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.987	R_int = 0.024
5200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.213	H-atom parameters constrained
S = 1.11	Δρ_max = 0.61 e Å⁻³
1858 reflections	Δρ_min = −0.47 e Å⁻³
136 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.0067 (2)	0.60204 (17)	0.30887 (18)	0.0406 (5)
O2	0.1226 (2)	0.62774 (19)	0.53341 (19)	0.0494 (6)
H2	0.1995	0.5993	0.5951	0.080*
C1	0.2147 (3)	0.4753 (2)	0.4208 (2)	0.0376 (6)
N1	−0.0869 (3)	0.8121 (2)	0.4675 (2)	0.0444 (6)
H1	−0.0212	0.7516	0.4899	0.080*
C10	0.1036 (3)	0.5752 (2)	0.4219 (3)	0.0361 (6)
O3	0.5211 (3)	0.1947 (2)	0.4273 (2)	0.0614 (7)
H3	0.5014	0.1663	0.3499	0.080*
C2	0.2031 (3)	0.4185 (3)	0.2978 (3)	0.0421 (7)
H2A	0.1256	0.4433	0.2149	0.080*
C8	−0.2648 (3)	0.9398 (2)	0.3478 (3)	0.0364 (6)
H8	−0.3401	0.9793	0.2727	0.080*
C7	−0.1811 (3)	0.8415 (3)	0.3413 (3)	0.0461 (7)
H7	−0.1880	0.8005	0.2611	0.080*
C4	0.4199 (3)	0.2872 (3)	0.4201 (3)	0.0438 (7)
C6	0.3317 (3)	0.4363 (3)	0.5424 (3)	0.0478 (7)
H6	0.3420	0.4738	0.6253	0.080*
C3	0.3048 (3)	0.3260 (3)	0.2973 (3)	0.0449 (7)
H3A	0.2960	0.2896	0.2143	0.080*
C5	0.4330 (4)	0.3435 (3)	0.5433 (3)	0.0545 (8)
H5	0.5102	0.3183	0.6262	0.080*
N2	−0.2226 (4)	0.9731 (3)	0.4821 (3)	0.0715 (9)
C9	−0.1105 (4)	0.8937 (3)	0.5572 (3)	0.0519 (8)
H9	−0.0586	0.8941	0.6528	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0403 (10)	0.0418 (10)	0.0347 (10)	0.0012 (7)	0.0099 (8)	0.0032 (7)
O2	0.0488 (11)	0.0549 (12)	0.0346 (10)	0.0151 (9)	0.0065 (8)	−0.0054 (8)
C1	0.0384 (13)	0.0386 (13)	0.0336 (13)	−0.0009 (10)	0.0121 (11)	−0.0003 (10)
N1	0.0458 (12)	0.0424 (12)	0.0412 (13)	0.0075 (10)	0.0137 (10)	0.0059 (10)
C10	0.0366 (13)	0.0371 (13)	0.0319 (13)	−0.0023 (10)	0.0108 (10)	0.0022 (9)
O3	0.0610 (13)	0.0710 (15)	0.0436 (12)	0.0277 (11)	0.0122 (10)	−0.0073 (10)
C2	0.0438 (14)	0.0463 (14)	0.0319 (13)	0.0046 (11)	0.0109 (11)	0.0005 (10)
C8	0.0331 (12)	0.0372 (12)	0.0323 (12)	0.0079 (10)	0.0065 (10)	0.0097 (10)
C7	0.0475 (15)	0.0476 (15)	0.0386 (14)	0.0003 (12)	0.0125 (12)	−0.0002 (12)
C4	0.0435 (14)	0.0466 (15)	0.0398 (14)	0.0068 (11)	0.0154 (12)	−0.0027 (11)
C6	0.0517 (16)	0.0551 (16)	0.0305 (13)	0.0116 (13)	0.0101 (12)	−0.0063 (11)
C3	0.0498 (15)	0.0503 (15)	0.0327 (13)	0.0049 (12)	0.0146 (12)	−0.0052 (11)
C5	0.0527 (16)	0.0673 (19)	0.0316 (14)	0.0177 (14)	0.0048 (12)	−0.0024 (13)
N2	0.075 (2)	0.0681 (19)	0.075 (2)	0.0103 (15)	0.0332 (17)	0.0024 (15)
C9	0.0572 (17)	0.0594 (18)	0.0343 (15)	0.0063 (14)	0.0137 (13)	0.0022 (12)

Geometric parameters (Å, º) top

O1—C10	1.269 (3)	C8—C7	1.330 (4)
O2—C10	1.249 (3)	C8—N2	1.358 (4)
O2—H2	0.8200	C8—H8	0.9300
C1—C6	1.387 (4)	C7—H7	0.9300
C1—C2	1.396 (4)	C4—C3	1.386 (4)
C1—C10	1.502 (4)	C4—C5	1.391 (4)
N1—C7	1.313 (4)	C6—C5	1.376 (4)
N1—C9	1.367 (4)	C6—H6	0.9300
N1—H1	0.8600	C3—H3A	0.9300
O3—C4	1.357 (3)	C5—H5	0.9300
O3—H3	0.8200	N2—C9	1.341 (4)
C2—C3	1.381 (4)	C9—H9	0.9300
C2—H2A	0.9300

C10—O2—H2	109.5	N1—C7—H7	125.9
C6—C1—C2	118.0 (2)	C8—C7—H7	125.9
C6—C1—C10	120.8 (2)	O3—C4—C3	123.1 (2)
C2—C1—C10	121.2 (2)	O3—C4—C5	117.4 (2)
C7—N1—C9	108.7 (2)	C3—C4—C5	119.4 (2)
C7—N1—H1	125.7	C5—C6—C1	121.5 (2)
C9—N1—H1	125.7	C5—C6—H6	119.3
O2—C10—O1	122.8 (2)	C1—C6—H6	119.3
O2—C10—C1	118.9 (2)	C2—C3—C4	120.1 (2)
O1—C10—C1	118.3 (2)	C2—C3—H3A	119.9
C4—O3—H3	109.5	C4—C3—H3A	119.9
C3—C2—C1	121.0 (2)	C6—C5—C4	119.9 (3)
C3—C2—H2A	119.5	C6—C5—H5	120.0
C1—C2—H2A	119.5	C4—C5—H5	120.0
C7—C8—N2	108.9 (2)	C9—N2—C8	106.8 (3)
C7—C8—H8	125.6	N2—C9—N1	107.3 (3)
N2—C8—H8	125.6	N2—C9—H9	126.3
N1—C7—C8	108.2 (2)	N1—C9—H9	126.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.527	3.057 (3)	120.73
N1—H1···O2	0.86	1.818	2.678 (3)	177.32
O3—H3···O1ⁱ	0.82	1.831	2.635 (3)	166.35
C8—H8···O1ⁱⁱ	0.93	1.886	2.748 (3)	153.18

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x−1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₇H₆O₃·C₃H₄N₂
M_r	206.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.601 (2), 10.530 (2), 10.586 (2)
β (°)	113.759 (3)
V (Å³)	979.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.47 × 0.29 × 0.10

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	5200, 1858, 1583
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.213, 1.11
No. of reflections	1858
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.47

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.527	3.057 (3)	120.73
N1—H1···O2	0.86	1.818	2.678 (3)	177.32
O3—H3···O1ⁱ	0.82	1.831	2.635 (3)	166.35
C8—H8···O1ⁱⁱ	0.93	1.886	2.748 (3)	153.18

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x−1/2, y+1/2, −z+1/2.

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Y2008B02 and Y2008B32).

References

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